Sodium borohydride → 3-Chlorobenzhydrol

HRID 1849881Notes

Reaction equation

HRID 1849881 reaction equation
C[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]([C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([Cl:16])[CH:11]=1)=[O:9].[BH4-].[Na+]>CCO>[Cl:16][C:12]1[CH:11]=[C:10]([CH:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:2]=2)[OH:9])[CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 13903332(3-Chlorophenyl)(2-methylphenyl)methanone

Product 1

HCID 5699073-ChlorobenzhydrolYield 94%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of methyl (3-chlorophenyl)(phenyl)methanone (1 g, 4.63 mmol) and sodium borohydride (352 mg, 9.26 mmol) in EtOH (6 mL) was stirred at 25° C. for 2 h. After removal of the solvent, the mixture was diluted with water (20 mL) and extracted with EtOAc (20 mL×3). The combined organic layers were washed with brine (20 mL), dried over anhydrous sodium sulfate, filtered and concentrated to give the desired product (950 mg, 94%) as yellow oil which was used in the next step without further purification.

Workup

  1. customAfter removal of the solvent
  2. additionthe mixture was diluted with water (20 mL)
  3. extractionextracted with EtOAc (20 mL×3)
  4. washThe combined organic layers were washed with brine (20 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-28f020a427474e459e19d223e3bfb270
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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